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The Last of the Sky Pirates by Paul Stewart (writer).

"The Last of the Sky Pirates" by Paul Stewart is the first book in the Rook trilogy which is part of the Edge Chronicles series. When Rook is chosen to continue his studies at Lake Landing, he sets out on the dangerous journey, facing many perils as he gains knowledge of many things in his world as well as his past. "The Last of the Sky Pirates" is an entertaining adventure that shows how this foundling becomes a hero.

While living in the Undertown sewers with the Librarian Academics, Rook dreams of becoming a librarian knight, chosen to continue his education at Lake Landing and search for the cure to stone-sickness, a mysterious ailment that ruins rocks' buoyancy and makes skysailing impossible. Rook is shocked when he is chosen, along with Stob and Magda. Disguised as merchants, Rook, Stob and Magda travel along the Great Mire Road where Rook helps free an imprisoned sky pirate, Deadbolt Vulpoon. They continue on through the Twilight Woods to the Eastern Roost where Hekkle disguises them as shrykes and leads them through the perilous Deepwoods to Lake Landing where they are joined by Xanth, a Guardian of Night disguised as an apprentice in order to spy on the Librarian Academics.

At Lake Landing, Rook, Stob, Magda and Xanth learn to build and control skycrafts, but Xanth breaks his leg during his first flight, preventing his continued studies. After completing his training, Rook accompanies Varis Lodd and Knuckle to the Foundry Glade where they free enslaved banderbears; however, Rook grows feverish after being struck by a poisoned arrow. During Rook's convalescence, Magda and Stob leave for their treatise-journeys, and Xanth visits Rook to apologize for setting Varis Lodd up to be captured at the Foundry Glade before he disappears since he has caused enough damage already. Healed, Rook leaves for his treatise-journey with the goal of finding the Great Convocation of Banderbears. He befriends Wumeru, a young banderbear, but she is upset when he follows her to the Great Convocation. The banderbears are ready to kill Rook until Wuralo, the banderbear he saved at the Foundry Glade, speaks up in his defense. Rook also meets Twig, a sky pirate captain, and when Twig mentions his friend, Cowlquape, Rook tells him that Cowlquape is being held prisoner at the Tower of Night.

Twig, Rook and a crew of banderbears retrieve the Skyraider, Twig's ship, from the Edgelands and sail to the Tower of Night. While Twig and the banderbears create a distraction by attacking the tower, Rook sneaks into the dungeons and rescues Cowlquape; however, his tether-rope gets snagged as he tries to flee. Xanth appears and orders Rook to stop, but recognizing his friend, he aims his arrow at the rope, freeing Rook. Rook rushes to the banderbears who have abandoned ship, but Twig has been mortally wounded and decides to die with his ship. At the last moment, a caterbird rescues Twig and flies away with him, presumably to take him to the restorative waters of Riverrise. While discussing how Varis Lodd found him, Rook realizes that a banderbear saved him when his parents were captured by slave-traders.